This invention relates to novel amino-substituted nitroimidazolyl-methyleneaminoimidazolidinones.
The effectiveness of nitroimidazoles against trichomonads has been known since the discovery of the antibiotic azomycin (2-nitroimidazole, S. Nakamura and H. Umezawa, J. Antibiotics [Tokyo], 9A, 66 [1955]). These and other 2-nitroimidazoles, however, have proved to be no better, in vitro, than metronidazole (see below) (G. C. Lancini, E. Lazzari, R. Pallanea, Il Farmaco Ed. Sc. 21, 278 [1966]), and the CD.sub.50 - and LD.sub.50 -values were considerably more unfavorable (E. Grunberg, E. Titsworth, Antimicrobial Agents and Chemotherapy 1965, 1966, 478). Only the 5-nitroimidazoles have, from a large number of synthesized compounds (C. Cosar, "Arzneimittelforschung" [Drug Research] 16, 23 [1966]), yielded an anti-trichomonial compound which is significantly effective in vivo, viz., metronidazole (5-nitro-2-methyl-1-(2-hydroxyethyl)-imidazole; see also French Patent No. 1,212,028), with a minimum inhibitory concentration of 2.5 .mu.g./ml. against Trichomonas vaginalis.
It has now been found that the condensation products of 1-alkyl-5-nitro-2-imidazolylcarboxaldehydes with 1-amino-2-imidazolidinones substituted in the 3-position with tert.-aminoethyl have approximately the same effective strength against Trichomonas vaginalis in the plate dilution test as metronidazole. Moreover, in contrast to metronidazole, marked blood levels become apparent after oral administration of the novel compounds. Thus, the novel compounds are also excellently suitable for the treatment of infections localized in the tissue.